EP0013078A3 - 1,2,4,5-Tetra-alkyl-4-arylpiperidines, their production and pharmaceutical preparations containing same - Google Patents
1,2,4,5-Tetra-alkyl-4-arylpiperidines, their production and pharmaceutical preparations containing same Download PDFInfo
- Publication number
- EP0013078A3 EP0013078A3 EP79302674A EP79302674A EP0013078A3 EP 0013078 A3 EP0013078 A3 EP 0013078A3 EP 79302674 A EP79302674 A EP 79302674A EP 79302674 A EP79302674 A EP 79302674A EP 0013078 A3 EP0013078 A3 EP 0013078A3
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- arylpiperidines
- tetra
- production
- pharmaceutical preparations
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
Compounds of formula
wherein
R¹ is hydrogen, hydroxy or methoxy,
R², R³ and R⁴ independently are C₁-C₅ alkyl;
R₀ is C₁-C₁₀ alkyl, benzyl or CH₂R⁶, in which R⁶ is C₂₋₇ alkenyl or C₃-C₆ cycloalkyl, the pharmaceutically acceptable acid addi tion and quaternary piperidinium salts thereof, are potent analgesics. Pharmaceutical formulations containing such compounds, a method for effecting analgesia, intermediates and a process for preparing such compounds, are provided.
R¹ is hydrogen, hydroxy or methoxy,
R², R³ and R⁴ independently are C₁-C₅ alkyl;
R₀ is C₁-C₁₀ alkyl, benzyl or CH₂R⁶, in which R⁶ is C₂₋₇ alkenyl or C₃-C₆ cycloalkyl, the pharmaceutically acceptable acid addi tion and quaternary piperidinium salts thereof, are potent analgesics. Pharmaceutical formulations containing such compounds, a method for effecting analgesia, intermediates and a process for preparing such compounds, are provided.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US965137 | 1978-11-29 | ||
US05/965,137 US4284635A (en) | 1978-11-29 | 1978-11-29 | Analgesic 1,2,4,5-tetra-alkyl-4-arylpiperidines |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0013078A2 EP0013078A2 (en) | 1980-07-09 |
EP0013078A3 true EP0013078A3 (en) | 1980-10-01 |
Family
ID=25509504
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP79302674A Ceased EP0013078A3 (en) | 1978-11-29 | 1979-11-22 | 1,2,4,5-Tetra-alkyl-4-arylpiperidines, their production and pharmaceutical preparations containing same |
Country Status (26)
Country | Link |
---|---|
US (1) | US4284635A (en) |
EP (1) | EP0013078A3 (en) |
JP (1) | JPS5573657A (en) |
KR (1) | KR830001214A (en) |
AR (1) | AR224138A1 (en) |
AT (1) | ATA750879A (en) |
AU (1) | AU529136B2 (en) |
BE (1) | BE880220A (en) |
CA (1) | CA1121357A (en) |
DD (1) | DD147537A5 (en) |
DK (1) | DK504979A (en) |
EG (1) | EG14137A (en) |
ES (2) | ES8101551A1 (en) |
FI (1) | FI793663A (en) |
FR (2) | FR2442836A1 (en) |
GB (1) | GB2038812B (en) |
GR (1) | GR72292B (en) |
HU (1) | HU178532B (en) |
IL (1) | IL58793A0 (en) |
IT (1) | IT1126406B (en) |
LU (1) | LU81923A1 (en) |
PH (1) | PH15420A (en) |
PL (1) | PL123672B1 (en) |
PT (1) | PT70486A (en) |
SU (1) | SU967275A3 (en) |
ZA (1) | ZA796336B (en) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5212183A (en) * | 1981-11-14 | 1993-05-18 | Basf Aktiengesellschaft | 4-(p-tert.-butylphenyl)-3-methylpiperidines substituted at the nitrogen, their quaternary salts and their use as fungicides |
US4485109A (en) * | 1982-05-07 | 1984-11-27 | E. I. Du Pont De Nemours And Company | 4-Aryl-4-piperidinecarbinols |
US4581456A (en) * | 1983-09-21 | 1986-04-08 | Eli Lilly And Company | Processes for preparing picenadol precursors and novel intermediates thereof |
ZW10287A1 (en) * | 1986-07-15 | 1988-01-13 | Hoffmann La Roche | Tetrahydronaphthaline and indane derivatives |
EP0299549A3 (en) * | 1987-07-09 | 1989-02-08 | Duphar International Research B.V | Tertiary 2,5-dialkyl-3-phenyl-piperidine derivatives having opiate-antagonistic activity |
CA1337418C (en) * | 1988-03-28 | 1995-10-24 | Engelbert Ciganek | 4-aryl-4-piperiding (or pyrrolidine or hexahydroazepine) carbinols and heterocyclic analogs thereof |
US5136040A (en) * | 1991-02-26 | 1992-08-04 | Eli Lilly And Company | Preparation of substituted tetrahydropyridines |
US5250542A (en) * | 1991-03-29 | 1993-10-05 | Eli Lilly And Company | Peripherally selective piperidine carboxylate opioid antagonists |
US5159081A (en) * | 1991-03-29 | 1992-10-27 | Eli Lilly And Company | Intermediates of peripherally selective n-carbonyl-3,4,4-trisubstituted piperidine opioid antagonists |
US5270328A (en) * | 1991-03-29 | 1993-12-14 | Eli Lilly And Company | Peripherally selective piperidine opioid antagonists |
GB9912411D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
GB9912415D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
GB9912417D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
GB9912416D0 (en) * | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
GB9912413D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
GB9912410D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2956058A (en) * | 1957-08-19 | 1960-10-11 | Lilly Co Eli | Novel substituted piperidines and pyrrolidines |
US3080372A (en) * | 1960-03-25 | 1963-03-05 | Res Lab Dr C Janssen | 1-aroylalkyl-4-arylpiperidine derivatives |
US3574219A (en) * | 1967-09-27 | 1971-04-06 | Tanabe Seiyaku Co | 1-(beta-hydroxyphenethyl)-2,3-dimethyl-3-(3-hydroxyphenyl)-piperidine |
FR2224457A1 (en) * | 1973-04-05 | 1974-10-31 | Ciba Geigy Ag | |
BE861930A (en) * | 1976-12-17 | 1978-06-16 | Rohm & Haas | INSECTIVE COMPOUNDS, ESPECIALLY FOR ARTHROPODS, AND THEIR APPLICATION METHOD |
US4115400A (en) * | 1976-05-27 | 1978-09-19 | Eli Lilly And Company | 1-Azoniabicyclo[3.1.0]hexanes |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2892842A (en) * | 1959-06-30 | Their preparation | ||
US3043845A (en) * | 1958-12-29 | 1962-07-10 | Abbott Lab | Phenylmethylpiperidine derivatives |
NL123743C (en) * | 1963-09-18 | |||
US3936468A (en) * | 1969-10-27 | 1976-02-03 | Sumitomo Chemical Company, Ltd. | Phenylbutanol derivatives |
AR206937A1 (en) * | 1974-09-06 | 1976-08-31 | Lilly Co Eli | PROCEDURE FOR PREPARING 1-SUBSTITUTE-4-ALKYL-4-PHENYL-PIPERIDINE COMPOUNDS |
-
1978
- 1978-11-29 US US05/965,137 patent/US4284635A/en not_active Expired - Lifetime
-
1979
- 1979-11-22 EP EP79302674A patent/EP0013078A3/en not_active Ceased
- 1979-11-22 ZA ZA00796336A patent/ZA796336B/en unknown
- 1979-11-22 PT PT70486A patent/PT70486A/en unknown
- 1979-11-22 AU AU53100/79A patent/AU529136B2/en not_active Expired - Fee Related
- 1979-11-22 FI FI793663A patent/FI793663A/en not_active Application Discontinuation
- 1979-11-22 GB GB7940422A patent/GB2038812B/en not_active Expired
- 1979-11-22 CA CA000340379A patent/CA1121357A/en not_active Expired
- 1979-11-23 FR FR7928977A patent/FR2442836A1/en active Granted
- 1979-11-23 BE BE1/9621A patent/BE880220A/en unknown
- 1979-11-23 IL IL58793A patent/IL58793A0/en unknown
- 1979-11-23 PH PH23322A patent/PH15420A/en unknown
- 1979-11-26 JP JP15349279A patent/JPS5573657A/en active Pending
- 1979-11-26 PL PL1979219885A patent/PL123672B1/en unknown
- 1979-11-26 LU LU81923A patent/LU81923A1/en unknown
- 1979-11-27 IT IT27614/79A patent/IT1126406B/en active
- 1979-11-27 EG EG708/79A patent/EG14137A/en active
- 1979-11-27 GR GR60608A patent/GR72292B/el unknown
- 1979-11-27 AT AT0750879A patent/ATA750879A/en not_active Application Discontinuation
- 1979-11-27 HU HU79EI892A patent/HU178532B/en unknown
- 1979-11-27 AR AR279039A patent/AR224138A1/en active
- 1979-11-28 DK DK504979A patent/DK504979A/en unknown
- 1979-11-28 ES ES486425A patent/ES8101551A1/en not_active Expired
- 1979-11-28 SU SU792847573A patent/SU967275A3/en active
- 1979-11-28 KR KR1019790004179A patent/KR830001214A/en unknown
- 1979-11-29 DD DD79217246A patent/DD147537A5/en unknown
-
1980
- 1980-05-13 FR FR8010755A patent/FR2453154A1/en active Granted
- 1980-07-31 ES ES493915A patent/ES8200664A1/en not_active Expired
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2956058A (en) * | 1957-08-19 | 1960-10-11 | Lilly Co Eli | Novel substituted piperidines and pyrrolidines |
US3080372A (en) * | 1960-03-25 | 1963-03-05 | Res Lab Dr C Janssen | 1-aroylalkyl-4-arylpiperidine derivatives |
US3574219A (en) * | 1967-09-27 | 1971-04-06 | Tanabe Seiyaku Co | 1-(beta-hydroxyphenethyl)-2,3-dimethyl-3-(3-hydroxyphenyl)-piperidine |
FR2224457A1 (en) * | 1973-04-05 | 1974-10-31 | Ciba Geigy Ag | |
US4115400A (en) * | 1976-05-27 | 1978-09-19 | Eli Lilly And Company | 1-Azoniabicyclo[3.1.0]hexanes |
BE861930A (en) * | 1976-12-17 | 1978-06-16 | Rohm & Haas | INSECTIVE COMPOUNDS, ESPECIALLY FOR ARTHROPODS, AND THEIR APPLICATION METHOD |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Designated state(s): DE GB NL SE |
|
PUAL | Search report despatched |
Free format text: ORIGINAL CODE: 0009013 |
|
AK | Designated contracting states |
Designated state(s): DE GB NL SE |
|
17P | Request for examination filed |
Effective date: 19810313 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN REFUSED |
|
18R | Application refused |
Effective date: 19831007 |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: ZIMMERMAN, DENNIS MICHAEL |